


Take a Step That Is New

by FagurFiskur



Series: Down at Our Rendezvous [2]
Category: Supernatural
Genre: Angel Siblings, First Meetings, Multi, Romantic Comedy, The threesome is mentioned not featured, Threesome - F/F/M
Language: English
Status: Completed
Published: 2014-02-14
Updated: 2014-02-14
Packaged: 2018-01-12 09:43:22
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,346
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1184736
Author URL: https://archiveofourown.org/users/FagurFiskur/pseuds/FagurFiskur
Summary: <blockquote class="userstuff">
              <p>Ruby's eyes lit up. "Hey! Speaking of amazingly hot threesome sex!" She stuffed her hand down her shirt and came back up with a small piece of paper. "It's Dean's number. I bullied him into giving it to me before he left." She handed the number to Castiel. "You should call him."</p>
<p>Castiel couldn't even begin to list the ways how terrible an idea that was. Mostly because he was busy thinking about Dean's sweet smile and chiseled upper body. And his eyes, those shining, green eyes, framed by thick eyelashes and how amazing would he look peering up at Castiel through those lashes...</p>
<p>Right. Terrible idea. He held the number out to Ruby. "I can't."</p>
            </blockquote>





	Take a Step That Is New

**Author's Note:**

> Starts pretty much where Come and Knock on Our Door ends. You don't need to read that one first unless you want to, just know that Ruby and Anna are dating and they picked up Dean together, which ended with Ruby pegging Dean.

When Dean woke that morning, it was in an unfamiliar place, aching in unfamiliar ways. It took him a couple of minutes to remember what had taken place the night before - seeing Anna's red head on the pillow next to him helped - and when he did, a sense of accomplishment he'd rarely felt washed over him.

Because seriously, if there was an accomplishment greater than having a threesome with a hot lesbian couple, Dean didn't want to hear about it. He also recalled with no small amount of pride that both women had seemed to enjoy themselves wildly. Anna, as a matter of fact, still had a satisfied little smile on her face, even as she slept. Dean would so be bragging about this later.

The pegging, he could go without mentioning. Or how much he'd liked it.

Which had obviously only happened because he was drunk.

But that had been last night and Dean was no longer drunk, just hung over. The smell of bacon wafting from the kitchen promised to settle his stomach, and Dean figured that he could go and grab a couple of strips before Ruby inevitably kicked him out. She didn’t really seem like the morning after type; Dean was honestly a little bit surprised that he hadn’t woken up on the curb outside the house.

Dean climbed out of bed, careful so as not to wake Anna, and fished his boxers off of the floor. He could worry about the rest of his clothes once he had filled his stomach. It wasn’t like he had anything to be ashamed about.

Dean padded quietly to the kitchen. He came to a short stop by the counter when he realized that the person standing over the pan was not Ruby, or a chick for that matter.

The stranger looked up and blinked, clearly stunned. His eyes dropped down to Dean’s bare chest and he reddened. “Who the hell-“

Before he could finish, Ruby walked out of what Dean assumed was the bathroom, drying her hair with a towel. “Morning, Cassie. Dean-o.”

Cassie – and Dean didn’t believe for one second that that was the guy’s real name, so he'd just refer to him by the much less embarrassing 'Cas' – turned his eyes to Ruby and glared. “Did you just cheat on my sister, in her own apartment?” His voice was low and growly and for one second, all Dean could think, absurdly enough, was ‘mother, may I?’.

Ruby rolled her eyes, unimpressed. “Chill it, Columbo. Anna was totally in on the fun. In fact, this whole hooking up with a stranger we met at a bar thing was her idea.” She smirked. “Don’t tell me you didn’t hear us. Dean here was very vocal.”

Dean flushed because, yeah, he had been. He glanced over to Cas, who looked even redder than Dean felt.

“I thought you were watching a pornographic film,” he finally muttered. He couldn’t seem to look either Dean or Ruby in the eye, staring instead straight at the sizzling bacon and eggs on the frying pan.

"Yeah, well," Ruby sighed. "I'd say sorry you had to hear that but one, you were supposed to be out and we had no idea you weren't and two..." she smirked, "Two, I'm gonna go out on a limb here and say that you didn't totally hate what you heard."

And great, now Dean couldn't look either of them in the eye either.

"I don't enjoy hearing my sister having sex," Cas protested.

Ruby snorted. "God, I should hope not. I know you guys are close but that would be too close for comfort. I was referring to the pretty noises Dean made. And possibly me." She quirked her head to the side and batted her eyelashes in a super affected way. "Let's face it, I'm pretty irresistible. It's okay to admit that you want me."

"Want you to leave," Cas muttered.

"Oh, fine, I'll leave you two alone." Dean shot Ruby a panicked look. No way was he up to spending any time with this stranger who apparently knew what he sounded like when he got fucked in the ass. This morning after was awkward enough already. Ruby, of course, ignored him. "Don't want Anna to wake up alone anyway, you know how cranky she gets in the morning."

Ruby stood up and stretched. "Better have some bacon ready when we get out of bed. Or just send Dean back in. Either way, I'm craving meat."

Yeah, Dean could never look that Cas guy in the face again. As soon as Ruby slammed the bedroom door shut behind her, an awkward silence descended. What the hell was there to say after a scene like that? Dean kept his eyes on the counter, drumming his finger softly.

Eventually, the silence became too much. "Do you want any help with that?" Dean asked lamely. He cringed at how hoarse his voice sounded; could it be any more obvious what he'd been doing? Not that Cas didn't already know.

"It's fine," Cas said. He clearly didn't want to continue the conversation, so Dean didn't press it.

The minutes stretched on and Dean seriously debated just going back to the bedroom as seeing what Anna and Ruby were up to but somehow that felt like it would be even more painfully awkward than the current situation, so he stayed put.

"I'm sorry," Dean said when he finally couldn't stay quiet anymore. "I had no idea that anyone else was home."

"It's fine," Cas repeated, sounding a little breathy with annoyance. "You had no way of knowing. I should have known better than to come back here when I knew my sister and her girlfriend would be having loud sex. I had intended to stay with my boyfriend but as it turned out, more people were having loud sex than just you three."

Dean's eyebrows flew up. "He was cheating on you."

"Apparently it was never an exclusive relationship," Cas said. "Somehow I failed to understand that." He stabbed at the finished bacon strips and slapped them on a plate with a lot more viciousness than was called for. "I also fail to understand why I am sharing this information with a complete stranger."

"Hey, sometimes it helps to talk." Dean shrugged. "Besides, it's not like we're complete strangers. You know what I sound like during sex, that practically makes us friends."

Dean didn't realize until after he had spoken that his little joke might backfire, that it might make Cas even more annoyed with him than he already was. He was inexplicably relieved when Cas let out a small chuckle.

"You have a strange way of making friends."

Dean smiled. "If you'd seen my o-face, you'd have attained BFF status."

Cas smiled back, a little sheepishly. "I'm sorry, I don't get that reference."

"What, BFF?" Cas nodded. "It means Best Friends Forever, or at least with teenage girls it does."

"I see."

The eggs and the rest of the bacon finished cooking and Cas turned off the stove. Dean helped him set the breakfast table, despite Cas's insistence that as a guest he shouldn't have to. Dean pointed out that he was an unannounced guest in Cas's home, and one that had probably cost him a great deal of a good night's sleep. Cas conceded that, adding that despite Dean being unannounced he certainly wasn't unwelcome, and let Dean help him.

"By the way, my name is Castiel. Not Cassie."

"Yeah, I figured it wasn't." Dean took a sip of orange juice. "Although I thought you'd be a Lucas or a Casper or something. I didn't see 'Castiel' coming."

"If you had, we would be BFF by now."

Dean nearly did a spit-take at that, causing Castiel to look inordinately proud. "Oh my God you asshole, you couldn't have waited until I had swallowed?" Cas raised an eyebrow and Dean started laughing. "Not a word."

Cas's big, blue eyes went even bigger. "I didn't say anything."

\---

In the end, Ruby and Anna didn't emerge from the bedroom until after Dean had left. Castiel had watched the other man go inside for his clothes (not that Cas could honestly say he minded his state of dress) and come back out fifteen minutes later, fully dressed and looking harried. He gave Castiel a warm smile as he left and Castiel felt a stab of loss at the thought that he might never meet the handsome stranger again. He had a way of talking that left Castiel at a complete ease and that wasn't common. It almost made him forget the fact that he knew what Dean sounded like when he climaxed (almost).

"Cas, I'm so sorry," Anna blurted as soon as she stepped outside the bedroom. "If I'd had any idea you were home-"

"Well, we didn't," Ruby said lazily. "So you've got nothing to be sorry about, Cassie here was the one who promised to stay at his beau's place for the night."

Anna frowned. "Why weren't you at David's place? Did you guys get into a fight?"

Castiel debated not telling her anything, leave it alone for a later time when he was better rested and could actually look his sister in the eye, but ultimately he knew that it wouldn't do any good to put it off. "No," he said truthfully. "But he was sleeping with someone else and we broke up."

"Oh my God," Anna exclaimed. "Are you serious?" Cas nodded. "That asshole is dead!"

"Do you want me to chop his balls off?" Ruby helpfully asked, making a scissoring motion with her fingers. "I can make it look like an accident."

"There's no need to kill David or... chop his balls off." Castiel sighed, circling his cup of coffee with both hands in a nervous gesture.

He hated these kind of talks, he never knew how he was supposed to act. Should he be hurt over David's betrayal? Maybe he was, a little bit, but the two of them hadn't been together for long and they hadn't been in love or anything. Castiel had never pictured them lasting. He was more angry than he was hurt, but he wasn't very angry either. Certainly not as angry as Anna looked to be.

"Our relationship was never exclusive," he continued. "It was just I who assumed it was. We broke it off because we realized we wanted different things."

"The guy's still an asshole," Anna insisted.

"Eh, I always knew he wasn't good enough for you," Ruby said with a shrug. Which was surprisingly sweet of her. Castiel was almost relieved when she completely ruined the sentiment with her next sentence. "I can't believe you're harshing my threesome buzz over this. What you should have done was go out and get laid immediately. No moping around the apartment while you listen to the people in the next room over having amazingly hot sex."

"Ruby," Anna chastised.

Ruby's eyes lit up. "Hey! Speaking of amazingly hot threesome sex!" She stuffed her hand down her shirt and came back up with a small piece of paper. "It's Dean's number. I bullied him into giving it to me before he left." She handed the number to Castiel. "You should call him."

Castiel couldn't even begin to list the ways how terrible an idea that was. Mostly because he was busy thinking about Dean's sweet smile and chiseled upper body. And his eyes, those shining, green eyes, framed by thick eyelashes and how amazing would he look peering up at Castiel through those lashes...

Right. Terrible idea. He held the number out to Ruby. "I can't."

Ruby scoffed, not accepting the small piece of paper back. "Why the hell not?"

"Forgetting the circumstances under which we met," Cas said, "Dean is straight."

"Like hell he is!" Ruby exclaimed. "No straight guy loves taking it up the ass so much."

Anna groaned and hid her reddening face in her hands. Meanwhile, Castiel's brain had short-circuited.

"I... What?"

"Yeah." Ruby nodded. "Dude totally let me peg him. Not just let, he loved every goddamn second of it. Those noises you heard didn't start until I was three fingers in, you know."

Castiel was fairly certain he was about to have a heart attack. "Thank you for the visual. But just because he likes... that, it doesn't have to mean he's anything other than straight."

"Fine." Ruby stood up and went to the couch, where her jacket lay crumbled. She shrugged it on. "Have it your way. Just know that you might be missing out big time if you don't give this dude a call. Come on, Anna. This bacon's cold and I'm craving some donuts."

Anna wordlessly nodded and followed her girlfriend out the front door, too mortified to say goodbye to Castiel.

The door slammed shut and Castiel was left alone in the apartment, Dean's phone number crumbled up in his right hand. Castiel knew he should throw it out. It wasn't like he was ever going to call it, no matter how charming or handsome or easy to talk to he'd found the other man.

It simply wasn't meant to happen.

\---

Dean was pretty sure that most people did not come out a threesome experiencing a crisis of sexuality. A devil's threeway, maybe, but not the regular kind. It wasn't as if he'd never done anything with another guy; he'd had his fair share of drunken fumbles, enough to know that sometimes, dick was his thing.

But giving someone a handjob or blowing them in a bathroom stall at a bar is one thing. Taking it up the ass is quite another and up until that threesome, Dean had never even considered it. The thought honestly hadn't entered his mind. He'd thought about fucking a guy a few times, but Dean Winchester did not bottom.

Except apparently sometimes he did. And apparently it made for the best sex of his life (well, that and the two hot bi chicks).

There was also Anna's brother, Castiel. Dean was a charming enough guy but he didn't have an easy time making friends. With Cas, though, they'd hit it off right away. Cas was witty in a dry and unconventional way, and he had this unique way of talking that sounded like he'd learnt to talk from books rather than human interaction. Which, okay, maybe wasn't the most flattering description, but Dean couldn't think of anything better. The dude was interesting and Dean liked talking to him. He was also kind of smoking hot.

If they had met under any other circumstance, Dean would have asked for his number. As it were, the circumstances involved Dean having sex with Castiel's sister and her girlfriend, and Castiel knowing what Dean sounded like when he took it up the ass. Not that Cas knew exactly what it was he'd been listening to (thank God), but it took Dean's mind to places. Places that were both terrifying and hot as hell.

This was not something Dean could handle alone. He needed to talk to someone and there was only one someone he knew that he felt comfortable telling everything that happened.

"I love this place," Charlie hummed happily around the coffee stirrer. "The caramel mocha is to die for."

It was a couple of hours before his shift at the Roadhouse and Dean had asked Charlie to meet at a coffee house. He'd made the mistake of letting her pick the place and here they were, in some fruity coffee shop slash bakery that looked like it'd been decorated by either an eight year old girl or an eighty year old woman. Lace and doilies and the color pink everywhere.

But the coffee was good and judging by the smell, the pastries were as well. Dean had ordered himself a slice of apple pie, which was currently in the oven. Charlie had decided to forgo a pastry since her large caramel mocha with whipped cream and chocolate sprinkles was quite enough to give her type two diabetes by itself.

Charlie finally stopped making love to the coffee stirrer and took a sip of her coffee, sighing blissfully. "So what did you wanna talk about?"

"I kind of, uh," Dean said, "I went to the bar last night and had a threesome with a lesbian couple."

Charlie wordlessly held up her hand, which Dean dutifully high fived. "Dude," she said. "I am so jealous I kind of want to drown you in my caramel mocha right now. How did you even manage that?"

"They were looking for someone and I happened to be the lucky one." Dean could totally do humble when need be. Besides, he needed to stay on Charlie's good side right now and bragging was not the right way to go about that. "But it kind of got out of hand."

Charlie raised an eyebrow. "Got out of hand? Dude, you were in a threesome with two, I'm assuming, smoking hot chicks." Dean nodded. "I don't see how anything could possibly go wrong in that scenario. Did they get too involved with each other and forget to get you off?"

"No," Dean said. He glanced around but the tables around them were empty and the nauseating music playing (was that Michael Bublé?) was enough to drown out their quiet voices. "It was going great and then one of them reached into the night stand and pulled out a strap-on."

"And you bolted," Charlie guessed. "Dude, that was like a once in a lifetime opportunity and you ruined it by being all scaredy straight boy..." She trailed off and Dean was suddenly aware of the fact that he was blushing. "No way."

"What?"

Charlie's eyes widened. "No way, you didn't run, did you? You stayed! You stayed and you got fucked up the ass."

And of course at that moment, the waitress arrived with Dean's pie. Worse yet, she looked like someone's grandmother. She put the plate down, gave Charlie a disapproving look and disappeared back into the kitchen.

"Wow, that was painful," Dean said.

"No changing the subject," Charlie chastized. She grinned. "Unless that was right on subject. Is it? I was right, wasn't I?"

Dean rubbed the back of his neck. "Yeah, you were."

"And?"

"And?"

Charlie threw up her hands. "Dude, you're impossible. How was it?"

"I... didn't hate it," Dean admitted. He knew Charlie could read between the lines and tell that 'didn't hate it' meant something else entirely.

"Oh my God," Charlie said.

"Just keep your voice down." Dean took a bite of his pie and almost dropped the fork as he had a spontaneous orgasm on the spot. Well, not really, but it was a near thing. "And for the record, it wasn't painful either."

"Okay, so you got pegged and you're freaking out," Charlie summarized. She took a sip of her coffee. "What am I supposed to say to help you with that? Some people just like taking it up the ass, there's nothing wrong with that."

Dean glared at her, swallowing his mouthful of pie. "So glad I decided to tell you about this. And there's more."

And so he told Charlie about Cas and the painfully awkward morning after, made all the worse by Ruby and her big mouth. Finally, reluctantly, he told her about how after a while, talking with Cas hadn't been awkward at all. It had actually been one of the more interesting conversations Dean had had in a while and now he maybe wished he could meet Cas again.

"I am so telling this story at your wedding," Charlie said when Dean finished speaking.

Dean scowled. "There's not gonna be a wedding, I'm never going to meet him again."

Charlie's eyes widened. "What? After a romantic first meeting like that? Okay, awkward as hell, but the fact that you guys could still talk after all that shows that you had a connection. Why would you let that go?"

"Well, I fucked his sister, for one," Dean said dryly. "A first meeting like that isn't something you just bounce back from. Besides, it's not like I have his number or anything."

"No, but you know where he lives," Charlie pointed out.

"And what am I gonna do with that information, stake out his apartment? I feel skeezy enough already about the whole thing."

Charlie rolled her eyes. "No staking out is required. Just pretend you forgot something at the apartment and drop by to pick it up. And then you ask him out for coffee, you hook up, live happily ever after and I get to make the greatest best man speech ever at your wedding."

"You know if I ever got married, Sam would be my best man," Dean said. He dropped his fork on the now empty plate. "And how could I be sure that he would be home and not, say, his sister?"

"Okay, good point." Charlie scratched her head. "What are you gonna do, then?"

"I already told you, nothing."

"Then why did you tell me all that, if not to get advice on how to proceed?"

That was a good question, one that Dean didn't really know the answer to. His thoughts had been a jumbled mess in his head, still were, and his first priority had been to word them out loud to someone who wouldn't mock him for them. But maybe he'd been hoping for advice, too. What else did he expect to get out of this? All he had right now was a headache.

"I don't know," he finally answered.

Charlie's expression softened. "Okay. It's fine, Dean, you don't have to know right now." She looked at her watch. "We should be heading back to work. But when you do figure out what you want, or at least what kind of help you want from me, I'm always here to talk."

Dean resisted the urge to metaphorically bury his head in the sand at being confronted with all those messy, girly emotions, and simply nodded curtly. "Yeah. Thanks."

"No problem."

\---

Castiel kept Dean's phone number but he didn't call it. He could practically feel it burning a hole in his wallet (yes, he kept it on him and he was well aware of how pathetic he was being) but the temptation to call never became too great. Certainly, he had enjoyed Dean's company and the other man was attractive enough - flipping gorgeous had been the term that Anna used and Castiel did not necessarily disagree.

But he and Dean had met under very unusual circumstances and while it may be possible for Castiel to look past that, he knew better than to expect that from Dean. After all, how many people would be willing to date someone whom they met through having a one-night-stand with their sister?

Yes, it was tempting to contact Dean but the thought of rejection kept Castiel from reaching into his wallet and dialing that number.

It was three weeks after meeting Dean that Castiel went to a local second-hand bookstore, Singer's Salvage Shop, picking up a birthday gift for Anna. He stopped short as soon as he walked inside because who should be sitting at the counter but Dean.

Of course. It seemed the universe had a sense of humor. It just so happened to be at Castiel's expense.

Castiel closed the door behind him and Dean looked up. Their eyes met from across the store and for a moment, Dean actually looked happy to see him. Then he flushed red and ducked his head, clearly remembering... well, everything from their last encounter.

Briefly, Castiel considered just leaving and coming back later, but Anna's birthday was tomorrow and he wouldn't have the time to pick up her gift then. Besides, who was to say that Dean wouldn't be working here tomorrow, too?

He walked up to the counter. "Hello, Dean."

"Cas," Dean muttered. Then, voice stronger, "Hey. You, uh, you need some help?"

"I'm picking up an order." Castiel was proud of how together he was. Everything about Dean, not just the way they met, seemed designed to leave him flustered. "William Goldberg's The Princess Bride? It should be under Milton."

Dean shot him a small smile (which most empathetically did not send Castiel's heart racing) and reached under the counter. "Yeah, I have it right here. Been in for a while, dude. Did Bobby not tell you when it would be delivered?"

Castiel felt his face heat slightly and hoped he wasn't blushing. "I've been busy."

Dean smirked, demeanor more confident now that Castiel was less so. "I'll bet."

The innuendo didn't make much sense, but the cheeky tone had Castiel even more flustered. He handed Dean his credit card, wanting to finish their transaction before he did or said something monumentally stupid.

But Dean beat him to it. "Do you wanna grab a coffee sometime?"

Okay, so it wasn't monumentally stupid so much as it was wonderful, but Castiel had presence of mind enough to know that had he liked Dean any less, he would have turned him down purely due to circumstance.

Fortunate that he liked Dean as much as he did. "I would like that."

Dean handed him back the credit card. His smirk had softened into a smile. "Yeah?"

"I like you," Castiel said, because he'd never bothered to learn to be anything other than direct. "And unfortunate circumstances aside, I would like to get to know you better."

Dean was silent for a moment. A light flush was making itself apparent on his cheeks. "Should I give you my number?"

"I have it." Castiel only realized afterwards how that might be taken. "Ruby," he added as an explanation.

"Oh." Dean wet his lips. "Right, that makes sense."

Castiel wasn't quite certain how to proceed. "I'll call you?"

Dean nodded. "Awesome."

Castiel took the book into his hand. It had been packed in brown paper and string, and the weight of it in his hand grounded him. He smiled, more confident. Echoed Dean's sentiment, "Awesome."


End file.
